


Dean's Bucket List of 'Naughty Things To Do with Castiel' - Part 5

by d_e_marcus



Series: Dean's Bucket List of Naughty Things To Do with Castiel [5]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Angel Sex, Angry Kissing, Angry Sex, Blow Jobs, Bottom Dean Winchester, Cock Rings, Dean Winchester Likes It Rough, Dean Winchester in Trouble, Doggy Style, Established Castiel/Dean Winchester, Face-Fucking, Fingerfucking, Gay Sex, Jealous Castiel (Supernatural), Jealousy, M/M, Plot What Plot/Porn Without Plot, Possessive Castiel, Rough Sex, Shameless Smut, Smut, Top Castiel, Top Castiel/Bottom Dean Winchester, Violent Sex, Wall Sex, angel grace, face down ass up
Language: English
Status: Completed
Published: 2019-02-04
Updated: 2019-02-04
Packaged: 2019-10-22 02:07:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,010
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17653997
Author URL: https://archiveofourown.org/users/d_e_marcus/pseuds/d_e_marcus
Summary: “I don’t share,” Castiel growls, grabbing Dean by the upper arm and squeezing hard enough to leave finger-shaped bruises.





	Dean's Bucket List of 'Naughty Things To Do with Castiel' - Part 5

**Author's Note:**

> This is a series that can be read as stand-alone fics, but they will contain mutual references, so it might be nice to read them in order.

Dean’s always liked his sex a little fast and a little rough. All those one-night stands he picked up in seedy bars, they liked it, too. But he could never just let go the way he wanted. Ladies don’t like bruises.

Now that he’s with Cas, though, things are different. He doesn’t have to worry about leaving marks, pounding too hard, or fucking too fast. He knows Cas can take it - he’s an _angel_ for Chuck’s sake - not only that, he _likes_ it. So yeah, Dean dishes it out….

But can he take it?

He sure wants to. Dean has watched Cas smite an entire army of demons, making heads roll and shredding bodies without so much as breaking a sweat. He’s thrown monsters across rooms and destroyed buildings. All of that angelic power on display...and not once has Cas rough-housed him in bed the way he truly wants.

Sure they’ve had rough sex when Cas was topping, but there was always the underlying note of restraint. _Calculated roughness_. Once, just once, Dean wants to be manhandled with all of the strength his angel possesses. He’s dreamed about it Chuck knows how many times and it’s sexy as fuck.

Maybe it’s wishful thinking or just a fucking bad idea, but that never bothered him before. Ever since Dean’s bucket list of ‘Naughty Things To Do With Castiel’ became a thing, he’s been checking sexcapades off left and right...except this one.

The first time Dean was injured in a hunt, it was passionate, but not rough. That one time he pissed Cas off? Rough, but it didn’t scratch the itch. When Dean did something stupid and almost got himself killed that one time? Well, that was pretty close.

On some level, Cas has to know that Dean wants it. He knows Dean better than anyone, Sammy included, and he can read Dean like a book. So why won’t he do it? Does Cas think he can’t take it? Does he think Dean will judge him? Or is Cas just holding back to spite him?

Dean wants Cas to fuck him so hard he hurts for a week — and there’s no way Cas doesn’t know that. In fact, the more Dean thinks about it, the more it pisses him off.

Turns out, the perfect cocktail is two parts whiskey, one part jealousy.

✽        ✽        ✽

The hunt was easier than expected. Dean left Sammy and Cas to deal with cleanup as he went back to the hotel to _tend to his wounds._ Sam just raised an eyebrow and said he’d get his own room for the night, bless him. Cas, none the wiser, agreed to meet Dean back at the hotel when they finished the job.

Dean rushed back to their room to shower and prepare himself for a most interesting evening. His plan isn’t well thought out, more of a rough draft with some loose ends, but damn if he ain’t going to use what Chuck gave him. He threw on a pair of dark wash jeans, a tight green henley that makes his biceps _and_ his eyes pop, and even put gel in his hair. 

Gel. In his hair.

Jesus, the lengths he’ll go to for a good dicking. 

Just thinking about it has him a little hot under the collar.

Dean pulls up at the popular college bar Google deemed the “best place for a good time” and parks his baby far away from any potential door-dingers. He thought about writing Cas a note with the name of the bar, but Castiel will be able to find him without it...eventually. Might as well have some fun with it.

After parking and checking the rear-view mirror one last time, Dean strolls through the door wearing that classic shit-eating grin he hasn’t used for some time.

Google wasn’t wrong. This place is crawling with ridiculously attractive college students and young professionals, perfect for tonight. Dean smirks at his good fortune...and the pretty blonde eyeing him from the bar. It’s showtime.

He leans against the bar next to her and waves the bartender over.

“Whiskey double, neat,” he says, casually ignoring the busty blonde bombshell. He slides onto his seat and takes a sip of the whiskey, relishing the way it burns down his throat.

“Drinking alone tonight?”

That didn’t take long. Dean tries not to wince at the high-pitched tone. Maybe he’s gotten too used to Cas’ rumbling baritone. 

He gives a noncommittal shrug, “For now.”

It’s not a lie. He’s alone now, yeah, but he won’t be in another 45 minutes or so. He’s just passing the time, keeping an eye on the clock until his blue-eyed angel storms through the door.

Barbie, surprisingly, doesn’t jump to fill the silence.

“How about you?” Dean asks, glancing over at her. She’s clearly beyond the age of a college student, but not yet 30, he thinks. Blonde hair in loose curls falls over her shoulders and her large brown eyes are warm and inviting. She probably works downtown in the marketing department of some nondescript company. Tasteful cleavage and showcase curves to boot. 

She smiles innocently, “For now.” 

Dean chuckles. He’s gotta hand it to her, she’s using his line as good as he ever did. It’s like meeting himself as a chick. Too bad he’s happily head over heels for an angel — five years ago he would have been smitten with her.

She holds out a delicate hand for Dean to shake, “My name’s Candice.”

“Candice” - yeah, totally not buying that - keeps him occupied through another twenty minutes and three whiskeys. She’s fun to talk to, flirts at all the right moments, knows when to use her voice and when to use her body. In other words, she’s a pro.

They face each other on the bar stools now, legs nearly touching, and just when things start getting interesting, Ken Doll shows up and slings an arm over her shoulder. He leans in to kiss her cheek as Dean struggles to control his surprise. Candice has been shamelessly flirting with him from the get go, so yeah, he’s a little stunned she’s got a model boyfriend and he’s _here._

Ken Doll finally notices Dean and turns toward him, his broad chest and shoulders just inches from Dean’s face, forcing him to look up at the man. He’s just as good looking as she is, now that Dean can unashamedly appreciate the male form.

Still doesn’t hold a candle to his angel though.

“Hi, I’m Chad.”

He doesn’t sound angry, but Dean doesn’t want the guy to throw a fit, so he flashes a smile and returns the shake good-naturedly.

Chad holds on just a beat too long as his eyes appraise Dean from the ground up, lingering too heavily on his lips.

Oh.

_Oh._

My, how the tables have turned. Dean glances between the two as they eye him thoughtfully and, dare he say, hungrily. Dean huffs an uncomfortable laugh and attempts to smirk, but he’s afraid it comes out more like an awkward grimace.

A predatory grin snakes across Candice’s face and for the first time tonight, Dean thinks maybe this wasn’t such a good idea. He wasn’t planning on the flirting going this far, just a few smiles and innocent conversation before Castiel would show up, undoubtedly looking rumpled and grouchy and gorgeous. He wanted to dance with him, show him off, maybe make him a smidge jealous from all of the stares.

Not like this.

His eyes stray from Candice to Chad, who’s slowly moving closer and boxing Dean in against the bar. A large, warm hand lands on his thigh, above the knee and definitely in the danger “this is a flirtation” zone. He stills under Chad’s touch, too shocked to move or protest.

Of all the people in here and he pulls in the swingers. Figures.

“So, Dean,” Chad asks huskily, “are you drinking alone tonight?”

Dean gulps, opening his mouth for some witty excuse to leave when —

“No, he’s not.”

Oh thank God, _Cas._

Castiel steps up behind Dean, a long line of heat against his shoulder that sends shivers down Dean’s spine. He closes his eyes and swallows against the titillation.

Surprisingly, Chad doesn’t seem the slightest bit discouraged, just intrigued. Both he and Candice look a little stunned, but the wheels are definitely turning as their eyes assess the newest addition to their _ménage à trois_.

Candice recovers first. 

“Well, I couldn’t have asked for a better birthday,” she purrs. “Who might you be, handsome?”

“Castiel,” he bites, his deep voice rumbling through Dean’s body as warm breath ghosts over his ear. If they don’t get out of here in the next five minutes, Dean is going to have the most awkward public boner ever. 

“Well, Castiel,” Chad joins in, “you came at the perfect time. Would you like to join us?" 

Whether he means for a drink or for the night, Dean’s not really sure, but the dude’s got balls.

Castiel is not impressed.

“I don’t share,” Castiel growls, grabbing Dean by the upper arm and squeezing hard enough to leave finger-shaped bruises.

Dean yelps when he’s pulled off the barstool. Candice and Chad - yeah, totally fake names - watch with wide eyes as Castiel drags Dean toward the back door. He shoots an apologetic look in their direction, hoping Candice finds another birthday present before the night’s out.

As he stumbles down the hallway, blood rushes through Dean’s ears, drowning out the noise of the bar, narrowing his focus to the sex-haired angel in front of him. The one with an iron grip on Dean’s bicep.

Before they reach the back door, Castiel swings Dean around until his back slams against the wall, knocking the wind from his body. Castiel’s eyes are alight with anger and a spark of fear courses through Dean.

A significant bulge in his jeans makes itself known.

“Were you going to leave with them, Dean?”

Dean gapes, so turned on he can’t begin to put letters together to formulate a response. Cas pulls him from the wall only to slam him right back into it, leaving him breathless again. Castiel’s hands clench around the front of Dean’s leather jacket, pulling him close.

“Did you think I wouldn’t see you?” Castiel’s leg presses between Dean’s thighs, pinning him to the wall.

“Cas,” Dean breathes, struggling for words. He thought Cas would be a little jealous, but not like this.

“Am I not enough for you, Dean?” Cas asks, his voice deep and ragged, filled with the anger that courses through him. Dean can _feel_ it, because it’s pushing in painfully against the bulge in his jeans. Dean understands the anger, but how in the hell could Cas believe he’d ever be anything less than perfect for Dean? This is not what he wanted, not at all. 

Dean’s pissed off, a little scared and...so very turned on.

“Cas, please, I wasn’t - ” Dean begins, ending on an exasperated note, “I was just talking to her Cas, I swear.”

“And yet, that man’s hand ended up on your leg,” Castiel growls. “He _touched_ you, Dean.”

Dean struggles in Castiel’s grip, attempting to remove himself from the wall and the leg from his manhood.

“Cas, I - ”

“YOU. ARE. MINE!” Castiel roars, his face inches from Dean’s, lips close enough to touch if Dean so wanted.

And oh does he.

Dean lurches forward, slamming his lips against Castiel’s mouth. Give Dean an inch and Castiel will take a mile — Dean might have initiated this kiss, but there’s no doubt who’s owning it. Castiel’s lips and tongue and teeth assault Dean relentlessly until he’s no longer a contributing participant. His mouth hangs open as he pants and takes Castiel’s retribution.

It vaguely occurs to him that they shouldn’t be doing this in the bar, where anybody could see them on their way to the bathroom. If Dean’s going to get his ass handed to him, it should at least be in private.

In an instant, it’s suspiciously quiet. When Castiel releases his mouth and Dean opens his eyes, the first thing he notices is that they are back in their hotel room. The second is the scowl and sex-hair Castiel is sporting. Dean’s eyes rake over Castiel’s face, taking in every line, every twitch, every blink. He’s a work of art.

Cas uses his silence and grabs him by the lapels to slam him into the nearest wall. A 1980’s era flower painting rattles somewhere near his head. Castiel crowds him, angled shoulders, hips and thighs pressing into every inch of Dean’s front.

Dean moans when Castiel’s thigh presses against the erection currently trapped in his jeans, and again when he feels the long, hard line of Castiel against him. The angel is enjoying this just as much as Dean is, apparently.

“You are mine, Dean Winchester,” Cas says with eerie calmness as his hands ruck up Dean’s shirt and scratch up his stomach to tug at his nipples. Dean cries out when Castiel twists both nipples, sending a shockwave of pleasure straight to his dick.

“Cas, please…” Dean begs. He’s so fucking hard it hurts.

With all of the blood rushing south to his Johnson, his brain is on lower power mode, so he can’t be blamed for not catching Castiel’s eyes narrowing and the look of understanding donning his face. It’s just something that’s happening, he sees it, but can’t process the meaning. 

Long, capable fingers reach for his waist, pulling his belt open and popping the button on his pants so forcefully that Dean’s hips snap back and forth with the force of it; he’s completely at Cas’ mercy and loving every second of it.

Dean is divested of his clothing in a matter of seconds and reduced to a quivering mess not long after. Not once has Cas let up, giving him a chance to catch his breath or hell, even participate. There are lips and hands and teeth all over his body, ratcheting up his sensitivity to a concerning degree.

Dean trembles with nerves and arousal until Cas steps back suddenly, leaving him open, bare and empty. He whines with the loss, sounding pathetically needy.

“Oh, Dean,” Cas breathes, sounding a tad bit smug, “look how you ache for me.”

Dean grunts when Castiel nips at his bottom lip, already plump from earlier attentions.

“So desperate,” he rumbles. “And I’m just getting started.” 

A filthy, filthy promise.

When Dean’s eyes finally regain focus, an amused smirk lingers on Castiel’s plump pink lips. Cas’ hair is artfully rumpled, his tie askew in his apparent haste to rid himself of the trenchcoat Dean’s become so fond of. He watches as Cas’ hands slowly loosen the tie and toss it on the bed, his fingers skimming down to open the top two buttons on his dress shirt and continuing down to his dress slacks.

What a sight they must make — Dean completely naked and flush to the wall with Cas still wearing most of his suit, his large, thick cock hanging out of the front of his pants, just waiting for Dean’s mouth. Perhaps it’s the sight of Cas looking so goddamn powerful (or the slight pressure on his shoulders) that makes Dean drop to his knees. 

He stares at Cas’ beautiful dick, licking his lips in anticipation. He leans forward, mouth open and ready, before Cas’ hand catches his chin, pulling his face up until Dean’s eyes snap up to his bright blue ones. Cas shakes his head, making a ‘tsk’ sound at Dean, before he reaches down to stroke himself.

“No, Dean,” Cas commands huskily, “you don’t deserve it yet.”

His fingers clamp down on Dean’s jaw and chin, holding him in place while he strokes himself, grunting occasionally. He forces Dean to watch him masturbate literally right in front of him and it’s the hottest thing Dean’s ever seen.

A wet dream come true.

Cas’ orgasm is so unexpected, Dean flinches when the first bit of cum lands on his nose. He closes his eyes, feeling the warmth landing across his cheekbones, his lips, his chin, until he’s dripping with the proof of Castiel’s pleasure. His tongue slides across his lips, tasting, before he looks back up at Cas. 

Dean really shouldn’t be surprised, really, but Cas is still fucking rock hard. Damn angel libido. 

Cas pushes his hips forward, the head of his cock brushing across Dean’s mouth, smearing the cum from his cheeks across his lips and back again. He continues this, using Dean’s perfect cock-sucking lips as he pleases before putting a slight bit of pressure on Dean’s bottom lip. When Dean opens to take Castiel’s cock inside of his tight, slick mouth, they both moan — one in pleasure, one in excruciating need. 

They’ve never done this before, but Dean can guess what’s coming. He takes a deep breath through his nose and closes his eyes while he attempts to relax his throat. Castiel’s fingers weave into his hair and tug sharply before he slowly begins to work his hips back and forth, fucking Dean’s mouth slowly. 

Castiel keeps going, increasing both the pace and the depth every few minutes until he’s fucking Dean’s mouth with abandon. Dean’s jaw aches, his lips are tender, tears prick at the corner of his eyes, and he loves every fucking minute of it.

Dean moans when Castiel spills into his mouth, swallowing down what he can, the rest leaking out the corners of his mouth until he can swipe it up with his tongue when Castiel pulls back.

They both pant with exertion, eyes locked on each other until Castiel reaches out to thumb across Dean’s cheekbone and down to his mouth, tugging his bottom lip from his teeth. The cum disappears from his face.

“Mine,” Castiel growls, grabbing Dean under the arms and hauling him up. Cas presses him against the wall again and Dean hazily wonders if he’s discovered a secret kink. He puts that thought aside for another time because he still hasn’t come and he’s so hard he could probably balance a book on the end of his dick.

“Yeah, Cas _..._ yours _._ ”

Cas snakes an arm around his stomach and another under his leg, hoisting him up until his legs are wrapped around Castiel’s waist and he’s pinned to the wall by sharp hip bones. He hooks his ankles together and cries out when teeth pinch the muscle between his neck and shoulder.

“Did you want me to see you with that woman? Did you want me to see another man touching you?” Castiel asks as an inexplicably lubricated digit circles Dean’s hole.

Dean’s dreamed about it so many times and yet, his wildest fantasies don’t hold a candle to this.

A thick finger breeches him, sliding in and out a few times before a second is added. The stretch burns.

“Cas, p-please…” Dean whimpers.

Cas’ fingers continue invading his tight hole as teeth nip at his neck, collarbones and bottom lip. Dean pants through the pleasure and the pain.

“Is this what you wanted, Dean?” Cas asks as his fingers stroke and prod Dean’s prostate. 

“Fuck!” 

Cas’ fingers retreat, Dean’s ass clenching around nothing, desperate to be filled once more. Those strong arms wrap around Dean’s waist so that Cas’ hands are firmly planted on Dean’s ass cheeks, effectively trapping his thighs to the sides of Cas’ body. There’s pressure pushing at his hole and he gasps in anticipation, but Castiel doesn’t penetrate him. 

“Did you want to make me jealous, Dean?” 

“Cas, please fuck me, _please_ ,” Dean begs. He’s so awash in the pleasure and pain that he can’t stop babbling. “I can’t take it, please, I - I need you. Cas, please _. Plea - ”_

“You are mine, Dean,” Cas growls as he pushes his cockhead against Dean’s puckered entrance. “I’m going to remind you of that.” 

“Jesus, _fuck_ , Cas!” Dean screams as Cas spears into him. 

Castiel pushes and pushes until he's balls deep inside Dean in one unyielding thrust.

“Holy fucking shit,” he pants through the pain. Dean knows that Cas could take the pain away, make him feel nothing but pleasure, but he also knows Cas isn’t going to do that. Dean needs to be taught a lesson and they both know it. 

The pain of being split open on Cas’ cock, his muscles straining in the position, his back scraping against the wall — it's everything. He _lives_ for it.

Cas starts to move and Dean knows there’s no turning back from here — that Cas is going to fuck him until he begs for mercy, until he definitely won’t be able to sit tomorrow, until feeling Cas’ punishment for days is a guarantee. 

There’s nothing he can do but hold on to the angel’s shoulders and take the pounding.

Cas fucks Dean against the wall like it’s the last thing he’ll do on this green Earth. He pounds into Dean’s tight hole over and over again, aiming for his prostate every other thrust, until Dean cries out.

“Cas, _fuck_ , I’m going to - ”

Just as Dean’s orgasm crests, it is ripped away from him by fingers circling the base of his cock and clamping down. 

“Oh, God no, Cas please,” Dean begs. “I need to come, please Cas, I can’t - ” 

“You’ll come when I let you.” 

Any further argument is abruptly cut off when Castiel angles his hips and nails Dean’s prostate one, two, three more times until he stills and comes inside Dean. Dean can feel every pulse of Cas’ cock, painting his insides and if he didn’t have this makeshift cock ring, that alone would have sent him over the edge.

Castiel withdraws from Dean’s ass, his cum leaking out of Dean’s hole, leaving him feeling sloppy, used and open.

Cas turns and Dean bounces on the bed before landing with a thud. 

Strong hands grip his waist tight enough to bruise then he’s flipped over onto his stomach, his hips pulled up until his ass is in the air, waiting to be filled. Castiel is most definitely using his grace to maintain his impressive erection because between one breath and the next, Dean’s ass is filled with it again. 

Cas pulls back as far as he can, then snaps his hips to slam his cock back into Dean’s tight little hole. He sets a relentless pace, his cock stretching Dean’s hole and dragging against his prostate. One hand steadies Dean’s hips as the other grabs onto the back of his neck and shoves his face down against the bedspread. 

Belatedly, Dean realizes that Cas’ hands are occupied, so that cock ring still clamped around his dick is angel grace — they certainly didn’t have a real one lying around in reaching distance. It’s - God, it’s so fucking hot, and Dean moans like a wanton whore at the thought of it.

In this moment, he exists for Cas and Cas alone, to be used how he pleases, to reaffirm that Dean _belongs_ to Cas. 

“Fuck, fuck, _fuck_ ,” Dean grunts with every thrust. “Holy fuck, Cas, please!” 

The babbling starts again. Dean is strung out, practically weeping from over-stimulation and he needs to come before his dick explodes. He’s so keyed up that this orgasm is going to be more painful than anything else. Castiel must understand his pleas are unjokingly serious because he picks up the pace, bucking wildly into Dean as he releases that iron grip of angel grace from Dean’s cock. 

Dean cries out as he comes, back arching and fists clenching in the sheets as white-hot sparks light him up from the inside. Cas stills when Dean’s tight hole starts clenching around him, emptying his last and final release inside of Dean. 

Cas pulls out gently, turning Dean on his side and gathering him up in his arms in a warm, protective cocoon. Dean is on the edge of sleep when he feels Castiel bite the back of his neck and murmur, “You’re mine.” 

“Yeah, Cas,” Dean whispers, “Yours.” 

He’s never felt more exhausted or more loved.

**Author's Note:**

> This post has not been beta'd. If you notice any mistakes, please let me know!
> 
> If you like Dean's Bucket List and want to see more, leave some kudos, comments or suggestions!


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